diff --git a/surfsense_backend/app/users.py b/surfsense_backend/app/users.py
index ee07ba88f..81d073559 100644
--- a/surfsense_backend/app/users.py
+++ b/surfsense_backend/app/users.py
@@ -2,7 +2,7 @@ import logging
 import uuid
 
 import httpx
-from fastapi import Depends, Request, Response
+from fastapi import Depends, HTTPException, Request, Response
 from fastapi.responses import JSONResponse, RedirectResponse
 from fastapi_users import BaseUserManager, FastAPIUsers, UUIDIDMixin, models
 from fastapi_users.authentication import (
@@ -180,6 +180,32 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
     ):
         print(f"Verification requested for user {user.id}. Verification token: {token}")
 
+    async def authenticate(self, credentials):
+        """
+        Override to return a specific error when user account doesn't exist,
+        instead of a generic LOGIN_BAD_CREDENTIALS.
+        """
+        from fastapi_users.exceptions import UserNotExists
+
+        try:
+            user = await self.get_by_email(credentials.username)
+        except UserNotExists:
+            # Still hash the password to mitigate timing attacks
+            self.password_helper.hash(credentials.password)
+            raise HTTPException(
+                status_code=400,
+                detail="LOGIN_USER_NOT_FOUND",
+            ) from None
+
+        verified, updated_password_hash = self.password_helper.verify_and_update(
+            credentials.password, user.hashed_password
+        )
+        if not verified:
+            return None
+        if updated_password_hash is not None:
+            await self.user_db.update(user, {"hashed_password": updated_password_hash})
+        return user
+
 
 async def get_user_manager(user_db: SQLAlchemyUserDatabase = Depends(get_user_db)):
     yield UserManager(user_db)
diff --git a/surfsense_web/lib/auth-errors.ts b/surfsense_web/lib/auth-errors.ts
index ce50c9c99..c761e41f8 100644
--- a/surfsense_web/lib/auth-errors.ts
+++ b/surfsense_web/lib/auth-errors.ts
@@ -45,6 +45,10 @@ const AUTH_ERROR_MESSAGES: AuthErrorMapping = {
 		title: "Invalid credentials",
 		description: "The email or password you entered is incorrect",
 	},
+	LOGIN_USER_NOT_FOUND: {
+		title: "Account not found",
+		description: "No account exists with this email address. Please sign up first.",
+	},
 	LOGIN_USER_NOT_VERIFIED: {
 		title: "Account not verified",
 		description: "Please verify your email address before signing in",
@@ -139,6 +143,7 @@ export function getAuthErrorMessage(errorCode: string, returnTitle: boolean = fa
 	if (!errorInfo) {
 		const patterns = [
 			{ pattern: /credential|password|email/i, code: "LOGIN_BAD_CREDENTIALS" },
+			{ pattern: /not found|no account|does not exist|user not found/i, code: "LOGIN_USER_NOT_FOUND" },
 			{ pattern: /verify|verification/i, code: "LOGIN_USER_NOT_VERIFIED" },
 			{ pattern: /inactive|disabled|suspended/i, code: "USER_INACTIVE" },
 			{ pattern: /exists|duplicate/i, code: "REGISTER_USER_ALREADY_EXISTS" },